[ CAS No. 871329-82-7 ] {[proInfo.proName]}

Name: 871329-82-7|(3-Fluoro-5-hydroxyphenyl)boronic acid|98%
Brand: Ambeed
SKU: A157116
Price: 7.0 USD
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Quality Control of [ 871329-82-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 871329-82-7 ]

SDS Specification

Alternatived Products of [ 871329-82-7 ]

Product Details of [ 871329-82-7 ]

CAS No. :	871329-82-7	MDL No. :	MFCD07363778
Formula :	C₆H₆BFO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RMBFBZIEXCTPDB-UHFFFAOYSA-N
M.W :	155.92	Pubchem ID :	44717308
Synonyms :

Calculated chemistry of [ 871329-82-7 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	3.0
Molar Refractivity :	38.25
TPSA :	60.69 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.85 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.57
Log Po/w (WLOGP) :	-0.37
Log Po/w (MLOGP) :	0.09
Log Po/w (SILICOS-IT) :	-0.77
Consensus Log Po/w :	-0.1

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.5
Solubility :	4.89 mg/ml ; 0.0314 mol/l
Class :	Very soluble
Log S (Ali) :	-1.42
Solubility :	5.97 mg/ml ; 0.0383 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.98
Solubility :	16.4 mg/ml ; 0.105 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.85

Safety of [ 871329-82-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 871329-82-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 871329-82-7 ]
Downstream synthetic route of [ 871329-82-7 ]

[ 871329-82-7 ] Synthesis Path-Upstream 1~1

1
[ 609807-25-2 ]
[ 871329-82-7 ]

Yield	Reaction Conditions	Operation in experiment
430 mg	With boron tribromide In dichloromethane at 0 - 20℃; for 3 h; Inert atmosphere	To a stuffed solution of (3-fluoro-5-methoxy-phenyl)boronic acid (500 mg, 2.942 mmol) in DCM (15 mL) was added 1 M solution of boron tribromide in DCM (14.7 mL, 14.7 mmol) under nitrogen atmosphere at 0 °C. The reaction mixture was stirred at RT for 3h. The reaction was monitored by TLC. After completion of reaction, the mixture was concentrated under reduced pressure. Water (15 mL) was added to the residue and the pH of the mixture was adjusted to 2 by the addition of 1M HC1 (aq.). The product was extracted with EtOAc (2x25 mL). The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford (3-fluoro-5-hydroxy-phenyl)boronic acid (430 mg) as an off-white solid.

Reference： [1] Patent: WO2015/58084, 2015, A1, . Location in patent: Paragraph 0222

[ 871329-82-7 ] Synthesis Path-Downstream 1~88

1
[ 1014720-89-8 ]
[ 871329-82-7 ]
[ 1061750-32-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃; for 6h;	Intermediate 18: N-[2-(3,5-Dimethyl-pyrazol-l-ylV6-(3-fluoro-5-hydroxy-phenyl)- p yrimidin-4- yl] -acetamide; To a solution of Intermediate 2 (5.7 mmol, 1.5 g) in dioxane (30 mL) and water (3 mL) was added <strong>[871329-82-7](3-fluoro-5-hydroxyphenyl)boronic acid</strong> (8.5 mmol, 1.3 g) and potassium carbonate (6.8 mmol, 950 mg). The solution was degassed with nitrogen for 5 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.06 mmol, 60 mg) was added and the mixture was heated at 100 0C for 6 hours. Once cool, the reaction was diluted with water and filtered. The solid filter cake was triturated with ether (100 mL) to yield the title compound (1.7 g, 87percent) as a light brown solid. LCMS (Method 3) m/z 341.8 [MH+], Tr = 2.57 min.

Reference： [1]Patent: WO2008/116185,2008,A2 .Location in patent: Page/Page column 50
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 5402 - 5405

2
[ 3934-20-1 ]
[ 871329-82-7 ]
[ 1354566-56-5 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 169 - 196

3
[ 871329-82-7 ]
[ 1354567-80-8 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 169 - 196

4
[ 871329-82-7 ]
[ 937270-81-0 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 169 - 196

5
[ 871329-82-7 ]
[ 1354566-73-6 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 169 - 196

6
[ 871329-82-7 ]
[ 1393180-79-4 ]
[ 1393180-92-1 ]

Yield	Reaction Conditions	Operation in experiment
31%	With cesium fluoride;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; water;Reflux;	Example 1533-(4-amino-1-((1-phenyl-1H-benzo[d]imidazol-2-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-5-fluorophenol 153A mixture of 3-iodo-1-((1-phenyl-1H-benzo[d]imidazol-2-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine 141 (1.0 g, 2.14 mmol), <strong>[871329-82-7]3-fluoro-5-hydroxyphenylboronic acid</strong> (0.4 g, 2.56 mmol), Pd(dppf)Cl2 (0.2 g) and CsF (0.65 g, 4.3 mmol) in DME (20 mL) and H2O (2 mL) was refluxed overnight. Then the mixture was cooled to room temperature, added H2O (50 mL) and extracted with EtOAc (20 mL.x.3). The combined organic layers were washed with brine, dried over Na2SO4 and then concentrated in vacuo. The residue was treated with CH2Cl2 and filtered to give 153 (300 mg, yield 31percent) as a grey solid. LCMS (ESI), M+H+=450.16. 1HNMR (400 MHz, DMSO) delta 5.795 (s, 2H), 6.606-6.633 (d, J=10.8 Hz, 1H), 6.720-6.724 (d, J=8.8 Hz, 1H), 6.800 (s, 2H), 7.065-7.083 (d, J=7.2 Hz, 1H), 7.213-7.260 (m, 2H), 7.400 (s, 5H), 7.657-7.676 (d, J=7.6 Hz, 1H), 8.119 (s, 1H), 10.139 (s, 1H)

Reference： [1]Patent: US2012/202785,2012,A1 .Location in patent: Page/Page column 260-261

7
[ 73781-91-6 ]
[ 871329-82-7 ]
[ 1417792-34-7 ]